CAREER ADVICE. Taleb in THE BLACK SWAN has a brief section where he gives advice, which differs somewhat from Ben Stein’s advice. He suggests a barbell strategy: avoiding or insuring against situations where there is a small chance of big losses and a large chance of small gains and looking for the possibility of Black Swans, a small chance of an enormous return. This is somewhat similar to Ben Stein. But Taleb recommends against choosing a profession where there are a few giants and a large number of dwarves.
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When I was young, one of the biggest mistakes I ever made was trying to avoid mistakes. Instead of taking chances, I was much too fearful and conservative. That’s one of the reasons why I have a useless Ph.D but have not been published yet. On the other hand, the writing I do now is a lot better, I think, than I could have done when I was young. Still, I think when you’re young, you can afford to fail at some things and learn about yourself and the world from the outcome of your ventures.